ex4-4.htm


    Exhibit
4.4

    IR
BIOSCIENCES HOLDINGS, INC.

     

    AMENDMENT
NO. 2

    to

    SECURED
CONVERTIBLE DEBENTURE DUE MAY 31, 2011

    


    THIS
DEBENTURE AMENDMENT SHOULD BE ATTACHED TO THE

    ORIGINAL
DEBENTURE CERTIFICATE

    


    This
Amendment No. 2 to Secured Convertible Debenture (this “Amendment”) dated August
8, 2008 is issued in connection with Secured Convertible Debenture (No.
IRBO-1-1) (the “Debenture”) issued on June 12, 2008 by IR Biosciences Holdings,
Inc. (the “Company”) to YA Global Investments, L.P. (the “Holder”) in the
original principal amount of $1,000,000 and amended pursuant to Amendment No. 1
thereto.  Capitalized terms used but not defined herein have the
meaning given thereto in the Debenture.

     

    THIS CERTIFIES THAT, the
following amendments are hereby made to the Debenture:

     

    
      	
              ·  

            	
              The
      Fixed Conversion
      Price shall be $1.50 (taking into effect adjustment due to the August 2008
      reverse stock split).

            


    

     

    
      	
              ·  

            	
              “Triggering
      Event” means the occurrence of any of the following: (i) June 30,
      2010, or (ii) a failure by the Company’s to achieve any of the Triggering
      Milestones.

            


    

     

    
      	
              ·  

            	
              The
      following Section 3(f) will be added to the
  Debenture:

            


    

     

    “Optional
Redemption at Election of Holder.  Subject to the provisions of this
Section 3(f), at any time and from time to time on or after December 31, 2009,
the Holder may deliver a notice to the Company (the date such notice is deemed
delivered hereunder, the “Optional Redemption Notice Date”) of its election to
compel the Company to redeem some or all of the then outstanding principal
amount plus the applicable Redemption Premium (such amount, the “Optional
Redemption Amount”) of this Debenture on the 5th Trading Day (such date, the
“Optional Redemption Date”) following the Optional Redemption Notice
Date.  The sum of all Optional Redemption Amounts with respect to this
Debenture and any Other Debentures shall not to exceed
$1,500,000.  The Optional Redemption Amount is payable in full in cash
on the Optional Redemption Date.  The Redemption Premium shall be
equal to twenty percent (20%) of the Principal amount being redeemed for a
Redemption made in accordance with this Section 3(f).”

     

    
      	
              ·  

            	
              The
      following Section 2(a)(x) will be added to the
  Debenture:

            


    

     

    “the
failure to pay the Optional Redemption Amount in full in cash on the Optional
Redemption Date.”

     

    
      	
              ·  

            	
              Section
      1(b) of each of the Debenture shall be removed in its entirety and
      replaced with the following:

            


    

     

    “Section
1(b) Payment of
Interest in Cash, Kind or Interest Debenture.

    


    
      	
              (i)  

            	
              From
      and after August 8, 2008, the Company shall pay interest to the Holder on
      the aggregate unconverted and then outstanding principal amount of this
      Debenture at the rate of 10% per annum, payable quarterly on March 31,
      June 30, September 30 and December 31, beginning on the first such date
      after the Original Issue Date, on each Conversion Date (as to that
      principal amount then being converted), and on the Maturity Date, or
      sooner as provided herein (each such date, an “Interest Payment
      Date”) (if any Interest Payment Date is not a Business Day, then
      the applicable payment shall be due on the next succeeding Business Day),
      either (A) in cash, (B) at the Company’s option, in duly authorized,
      validly issued, fully paid and non-assessable shares of Common Stock at
      the Interest Conversion Price (the dollar amount to be paid in shares, the
      “Interest Share
      Amount”), (C) at the Company’s option, by issuing an Interest
      Debenture for the amount of Interest being paid (in the form attached
      hereto as Exhibit II)
      (the “Interest
      Debenture”) in the aggregate principal amount equal to such
      interest amount, or (D) a combination thereof of (A), (B) and (C); provided, however, that
      payment, pursuant to subsection (B), in shares of Common Stock may only
      occur if (i) all of the Equity Conditions have been met (unless waived by
      the Holder in writing) during the 20 Trading Days immediately prior to the
      applicable Interest Payment Date (the “Interest Notice
      Period”) and through and including the date such shares of Common
      Stock are actually issued to the Holder, and (ii) the Company shall have
      given the Holder notice in accordance with the notice requirements set
      forth below; provided, further, however, if the
      Company shall determine to pay interest in the form of an Interest
      Debenture, attached hereto as Exhibit II, or
      in the form of shares of Common Stock, the Company shall deliver such
      Interest Debenture, registered in the name of the Holder and in the
      aggregate principal amount equal to such interest payment, or such shares
      of Common Stock, no later than three (3) Trading Days following the
      Interest Payment Date.

            


    

     

    
 

    
      
        
        

      

      
        
        

        
          

        

      

      
        
        

      

    

    
      	
              (ii)  

            	
              Company’s Election to
      Pay Interest in Cash, Shares of Common Stock or Interest
      Debenture.  Subject to the terms and conditions herein,
      the decision whether to pay interest hereunder in cash, shares of Common
      Stock, or in the form of an Interest Debenture, or a combination thereof,
      shall be at the sole discretion of the Company.  Prior to the
      commencement of any Interest Notice Period, the Company shall deliver to
      the Holder a written notice of its election to pay interest hereunder on
      the applicable Interest Payment Date either in cash, shares of Common
      Stock, an Interest Payment Debenture or a combination thereof, provided
      that the Company may indicate in such notice that the election contained
      in such notice shall apply to future Interest Payment Dates until revised
      by a subsequent notice.  During any Interest Notice Period, the
      Company’s election (whether specific to an Interest Payment Date or
      continuous) shall be irrevocable as to such Interest Payment
      Date.  Subject to the aforementioned conditions, failure to
      timely deliver such written notice to the Holder shall be deemed an
      election by the Company to pay the interest on the Interest Payment Date
      in cash.  At any time the Company delivers a notice to the
      Holder of its election to pay the interest in shares of Common Stock, the
      Company shall timely file a prospectus supplement pursuant to Rule 424
      disclosing such election, unless Company Counsel is able to provide the
      Transfer Agent with a Rule 144 opinion as to such
  shares.

            


    

    


    
      	
              (iii)  

            	
              Interest
      Calculations. Interest shall be calculated on the basis of a
      360-day year, consisting of twelve 30 calendar day periods, and shall
      accrue daily commencing on the Original Issue Date until payment in full
      of the outstanding principal, together with all accrued and unpaid
      interest, liquidated damages and other amounts which may become due
      hereunder, has been made.  Payment of interest in shares of
      Common Stock shall otherwise occur pursuant to Section 4(b) herein and,
      solely for purposes of the payment of interest in shares, the Interest
      Payment Date shall be deemed the Conversion Date.  Interest
      shall cease to accrue with respect to any principal amount converted,
      provided that, the Company actually delivers the Conversion Shares within
      the time period required by Section 4(b) herein.  Interest
      hereunder will be paid to the Person in whose name this Debenture is
      registered on the records of the Company regarding registration and
      transfers of this Debenture.

            


    

    


    
      	
              (iv)  

            	
              Late
      Fee.  All overdue accrued and unpaid interest to be paid
      hereunder shall entail a late fee at an interest rate equal to the lesser
      of 18% per annum or the maximum rate permitted by applicable law (the
      “Late
      Fees”) which shall accrue daily from the date such interest is due
      hereunder through and including the date of actual payment in
      full.  Notwithstanding anything to the contrary contained
      herein, if, on any Interest Payment Date the Company has elected to pay
      accrued interest in the form of Common Stock but the Company is not
      permitted to pay accrued interest in Common Stock because it fails to
      satisfy the conditions for payment in Common Stock set forth in Section
      1(b) herein, then, at the option of the Holder, the Company, in lieu of
      delivering either shares of Common Stock pursuant to this Section 1(b) or
      paying the regularly scheduled interest payment in cash, shall deliver,
      within three (3) Trading Days of each applicable Interest Payment Date, an
      amount in cash equal to the product of (x) the number of shares of Common
      Stock otherwise deliverable to the Holder in connection with the payment
      of interest due on the Interest Payment Date multiplied by (y) the highest
      VWAP during the period commencing on the Interest Payment Date and ending
      on the Trading Day prior to the date such payment is actually
      made.  If any Interest Conversion Shares are issued to the
      Holder in connection with an Interest Payment Date and are not applied
      against an Interest Share Amount, then the Holder shall promptly return
      such excess shares to the Company.

            


    

    


    
      	
              ·  

            	
              The
      definition of “Interest Payment Date” set forth in Section 17(n) shall be
      deleted and replaced with the
following:

            


    

     

    “‘Interest Payments
Date’ shall have the meaning set forth in
Section 1(b).”

     

    
      	
              ·  

            	
              The
      form of Interest Debenture attached as Exhibit II to that certain letter
      agreement dated August 8, 2008 shall be attached as Exhibit II to the
      Debenture.

            


    

     

    
      	
              ·  

            	
               The
      definition of “Equity Conditions” set forth in Section 17(i) shall be
      deleted and replaced with the
following:

            


    

     

    “Equity
Conditions” means, during the period in question, (a) the Company shall have
duly honored all conversions and redemptions scheduled to occur or occurring by
virtue of one or more Conversion Notices of the Holder, if any, (b) the Company
shall have paid all liquidated damages and other amounts owing to the Holder in
respect of this Debenture, (c)(i) there is an effective Registration Statement
pursuant to which the Holder is permitted to utilize the prospectus thereunder
to resell all of the shares of Common Stock issuable pursuant to the Transaction
Documents (and the Company believes, in good faith, that such effectiveness will
continue uninterrupted for the foreseeable future) or (ii) all of the Conversion
Shares issuable pursuant to this Debenture (and any shares issued in lieu of
cash payments of interest hereunder) may be resold pursuant to Rule 144, (d) the
Common Stock is trading on a Trading Market and all of the shares issuable
pursuant to the Transaction Documents are listed or quoted for trading on such
Primary Market (and the Company believes, in good faith, that trading of the
Common Stock on a Primary Market will continue uninterrupted for the foreseeable
future), (e) there is a sufficient number of authorized but unissued and
otherwise unreserved shares of Common Stock for the issuance of all of the
shares issuable pursuant to the Transaction Documents, (f) there is no existing
Event of Default or no existing event which, with the passage of time or the
giving of notice, would constitute an Event of Default, (g) the issuance of the
shares in question to the Holder would not violate the limitations set forth in
Section 4(c) herein, (h) there has been no public announcement of a pending or
proposed Fundamental Transaction that has not been consummated, and (i) the
Holder is not in possession of any information provided by the Company that
constitutes, or may constitute, material non-public information.

     

    
      
        
        

      

      
        
        

        
          

        

      

      
        
        

      

    

     

    IN WITNESS WHEREOF, the
Company has caused this Amendment to be signed by its duly authorized
officer.

     

    IR
Biosciences Holdings, Inc.

    


    By:       /s/ Michael
Wilhelm                 


    Name:  Michael
Wilhelm

    Title:    CEO